1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59868786, compound

HRID 383711Notes

Reaction equation

HRID 383711 reaction equation
N12CCCN=C1CCCCC2.Cl[C:13]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([N+:21]([O-:23])=[O:22])=[C:15]([O:24][CH3:25])[N:14]=1.Cl.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH2:35][NH:34][CH2:33][CH2:32]2>CN(C=O)C>[CH3:25][O:24][C:15]1[C:16]([N+:21]([O-:23])=[O:22])=[C:17]([O:19][CH3:20])[N:18]=[C:13]([N:34]2[CH2:33][CH2:32][C:31]3[C:36](=[CH:37][CH:38]=[C:29]([C:28]([F:27])([F:40])[F:39])[CH:30]=3)[CH2:35]2)[N:14]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109985372-Chloro-4,6-dimethoxy-5-nitropyrimidineHCID 217125586-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 59868786HCID 59868786, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (0.669 g, 4.4 mmol) was added to a mixture of 4a (0.438 g, 2 mmol) and 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.487 g, 2.05 mmol) in DMF (5 ml) at 0° C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 5b (0.76 g, 1.98 mmol, 99%).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. customchromatographed

Sources & evidence

ORD record
ord-e961be4534b04202857f7d81827130f4
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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